


Let Me Milk You Dry

by omgspnfanfiction



Category: Supernatural
Genre: Breast Play, Breastfeeding, Brother/Sister Incest, Couch Sex, Cowgirl Position, Dry Humping, Erotic Gif, Explicit Gif, Explicit Sexual Content, F/M, Feeding, Feeding Kink, Fluff and Smut, Grinding, Incest, Incest Kink, Milking, Multiple Orgasms, NSFW, NSFW GIF, Nipple Licking, Nipple Play, Orgasm from Breast Play, Original Character(s), Plot What Plot/Porn Without Plot, Quarantine, Reader-Insert, Riding, Sex, Sexual Content, Sibling Incest, Smut, Vaginal Sex, boobs, boobs full of milk, breast pain, juicing titties, porn gif, quarantine sex, riding sex, sex gif, sperm inside
Language: English
Status: Completed
Published: 2020-09-12
Updated: 2020-09-12
Packaged: 2021-03-07 00:20:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,432
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26417851
Author URL: https://archiveofourown.org/users/omgspnfanfiction/pseuds/omgspnfanfiction
Summary: Y/n is suffering from not being able to breastfeed her baby properly, breasts engorging, and needing to be milked. Dean being the caring big brother he is helps by milking her dry, it's not his fault if they both get so turned on it leads to more.
Relationships: Dean Winchester and Y/n - Relationship, Dean Winchester/Original Character(s), Dean Winchester/Original Female Character(s), Dean Winchester/Reader, Dean Winchester/Sister!Reader, Dean Winchester/You
Comments: 24
Kudos: 440





	Let Me Milk You Dry

**Author's Note:**

> I don’t know anything about how it feels to breastfeed or have pain, I assume being filled with milk or pain from it doesn’t last long either but in this fic it does. Crack fic. Don't read if incest makes you uncomfortable or squeamish

Another pathetic whimper leaves your lips as you shift for the millionth time, hoping that the throbbing will finally ease the more you move around. You didn’t even know your breasts could ache this way, but sadly your baby didn’t use all of your milk and that left you sore and way to full for comfort. Leaving you constantly leaking and needing to pump, missing the days your boyfriend was around to relieve your pain directly from the source. He left you and the baby a month before quarantine happened and you hadn’t been able to go out bar hopping looking for someone who would do you the favor, not that you wanted to do so either, feeling uncomfortable in your body since the baby.

Having your breasts played with was heavenly though and something you deeply desired, your own hands massaging your breasts didn’t feel nearly as good and you craved a firmer touch to help soothe your pain and pleasure you at the same time. It didn’t help that giving birth had heightened your senses a great deal and made breast play and everything else more enjoyable, especially since the slightest touch had you wet and ready these days.

“What’s wrong sweetheart?” Dean’s voice asked breaking through your pity party and pained groans, his confused but concerned face watching you massage your breasts.

“Nothing don’t worry about it.” You said trying to stop your actions and keep your hands off yourself.

“Come on, you know you can tell me anything.” He said taking a seat next to you on the couch, getting comfortable before giving you his full attention.

“Alright, it’s a little embarrassing, but my boobs are very tender right now and it's causing a lot of discomfort.” You say looking over at him but instead of meeting his eyes, you see he’s staring over your shoulder. He was never one to feel comfortable talking about anything related to your body or female issues, even though he always was there for you whenever you needed, talking about that stuff with his little sister still made him squirm.

“Um, oh, I’m sorry, is… is that normal?” Dean asks trying to be sensitive and supportive but feeling quite awkward about the topic, especially since your breasts had gotten noticeably bigger since having the baby and he had troubles looking away.

“You think I’d be moaning in pain if it were. No, the baby is just not drinking enough from me and I’m overfilling, so the build-up causes a lot of pressure and I can only pump so much out.” You say continuing to massage your sore breasts, not caring if Dean was in the room anymore as they hurt too much. His eyes were doing everything to try to avoid following your movements, but it was inevitable one quick slip of his eyes and they became glued to you.

“Does– does that help?” He asks completely hypnotized, the way they kept bouncing around as you felt yourself, squishing them together, it was almost a little show you put on just for him, one he knew should not have him as entranced as he was.

“Yeah, when my ex was around he would massage them every night for me. I didn’t realize how much it would help me out for him to suck on them and get rid of the milk.”

“He really drank from you?” Dean asks, his eyes going wide, you guessed he was more than likely grossed out by the thought or had no idea why anyone would do that outside of Busty Asian Beauties. Unaware that Dean was having quite the opposite issue as his pants got a little tighter, you had unknowingly brought out a kink he had or at least one he enjoyed masturbating to.

“I… I could do that for you. I can help.” He tells you, convincing himself that he is doing this to be a good big brother and wanting to help you out since that dickbag left. The selfish part of him knew that he wasn’t doing this to be a good brother but to get a taste of those enlarged tits he had secretly fantasized about.

“What, you want to suck the milk out of my nipples.” You say laughing a little thinking he was joking. He felt himself twitch hearing you say that aloud, he knew it wasn’t sexual and you genuinely needed relief but he still couldn’t stop the flood of images filling his head of what he would to you.

“Yeah, I know it sounds weird but hear me out. Helping you doesn’t mean anything besides a brother being there for his little sister. Who knows when we’ll be allowed to leave, let alone go to bars, and I can’t take the idea of you suffering when I know I could help.” He said ears turning red as he tried to convince you of the idea. You couldn’t deny you needed help and you weren’t going to be able to find it elsewhere for a while, god this was messed up and you were going straight to hell for thinking about it.

“But you’re my brother, it would be wrong.” You say confused but not saying no.

“It's not wrong Y/n/n. I just want to help you feel better, you know I hate seeing you in pain.” He said moving toward you, you didn’t stop him but didn’t go toward him either, still trying to wrap your mind around the turn of events. “Plus, it's only wrong if I fucked you and this is only about your tits”

“I don’t know Dean.” He ignores your words, placing his hands over yours and pushing them gently aside as he takes over, trying to match your movements. The soft sigh you let out, allows some of the tension to bleed from him at seeing you relax into his touch. When it was clear you weren’t rejecting him nor did it seem like you planned to, he continued, feeling you through your shirt and nursing bra.

“Dean, this… this isn’t right.” You say with no real conviction, your actions speaking louder as your body melts into him, enjoying the stimulation you needed for your aching breasts.

“Come on princess, you don’t even believe that. Now just relax for your big brother, I’m gonna take good care of you.” he said while applying pressure to his hands smiling at the little moans slipping from your lips. He gently began moving down to your shirt and tugging at it, understanding the signal you help him remove the obstruction. Showing your consent but murmuring about it just being for his help and nothing more. Not bothering to stop at just your shirt he continued with your bra while he was at it. Leaving you naked and flushed in front of him.

“Don’t even think about it.” he said stopping your hands before they could come out and hide your body from him.

“I just don’t look as good as I once did since the baby is all.” You say in response not baring to look in his eyes too afraid to see his reaction, even if he was just helping you out no one but your ex has seen you naked since the baby.

“Princess, you know you’ve always been the prettiest girl in the world and everything you think looks bad I love, trust me you're perfect, and if anything is different it's just to show how awesome you and your body are because they made that cute little bugger.” You had tears threatening to spill at his words, he was right though this was Dean, your Dean, your big overprotective brother who had done nothing but look after you and defend you, you had nothing to worry about. In true Dean fashion when things became too emotional, he said something that killed the moment two seconds later. Pinching your nipple, he adds “Plus, have you seen these tits, baby I haven’t been able to stop staring at them”

His words cause you to laugh as he knew they would and he smiles as he brings his hands back to your breasts, grasping onto them and continuing his administrations, looking like a kid in a candy store rather than a concerned brother helping out his youngest sibling. The feeling of his firm but calloused hands on your breasts, has you trembling, not able to prevent the reactions in your body as you felt the telltale signs of arousal start forming in your panties. It wasn’t just his talented hands that had you wanting to rub your thighs together either but the way he was staring at you in a sort of awed desire, it made you feel secure and confident, something you hadn’t necessarily felt since before the baby. Your hormones had been all over the place as had your emotions, or at least that’s the excuse you were going with to explain the wetness you were feeling in your panties, you wouldn’t feel that way otherwise for your brother. Not wanting it to be weird or uncomfortable you just clench your legs and ignore it, maybe you should’ve stopped but he was right this was just him helping you out. Being a good brother, not wanting to see you suffer, nothing else, especially nothing sexual. You just had to convince your body of that.

“De please.” You beg, needing more, the pressure was too much and feeling very uncomfortable even if his actions were releasing most of it, a new source of uncomfortableness had settled in.

Gently dropping his head to your breast, not removing his hands as he takes your right nipple between his lips. Before you can urge him along once more, he sucks it in his mouth and with his hand starts coaxing the milk out. You almost felt guilty for encouraging him to drink from you, but as soon as his lips touched you those thoughts left.

The first drops that hit his tongue had him sucking down harder, the taste surprising him but making him greedy for more. He manages to get a couple of mouthfuls, your hand in his hair pressing him against you, chasing the sensations. It felt amazing, the pressure was being relieved but seemed to be going straight to your clit. Getting tired of the awkward bend he had to do, his hands move to your waist pulling you forward, not letting his lips leave your boobs but pulling you onto his lap so you were straddling him, making it easier to nurse from you.

“Fuck.” You moan out, head leaning back as you arch into him, automatically your hips start undulating into his slowly, not enough to do much but slightly stimulate the two of you. Barely realizing that he was hard against your shorts from the suction. Lightly you tug on his hair to pull him away, but he resists not wanting to give up his treat. “De, it’s a little tender can you switch for a bit.”

He smiled up at you and switched over eagerly, almost forgetting he had another one to play with. “Of course, princess, anything you need to feel good I’m here for you, that’s what big brothers do.”

“Thank you, big brother, you’re the best, always looking out for me, making me feel sooo –” your words cut off by a moan as he clamps onto your other breast and immediately starts sucking on you. Unable to stop yourself from continuing to undulate your hips into his, you were so needy, you barely noticed you had been doing it since he sat you on his hips. It was hard not to though, his lips seemed to have a direct connection with your clit, every vibration, every lick had you closer to an orgasm. Not even when you had your ex suck on your tits were you this close to coming so soon after latching on, even with the extra sensitivity of your breasts it still took more than the ten minutes Dean had been touching you for.

Your legs gripped around his hips nestling him in closer to your body, it caused such pleasure to look down and see him so content eyes closed, sucking on you with no care in the world. While he looked so peaceful his actions were anything but, mouth never losing pressure, sucking like a man on a mission, swallowing every drop you released, hands slipping up and down your body coming close to your core but never touching you there. You didn’t even think he realized what he was doing, just letting himself go in a way you hadn’t seen in a long time.

Your hips never stop grinding into him, trying to get pressure on your clit directly. He starts matching your moves, moving his hips slowly into yours, his tented pants meeting you at every pace. Still too lost in your body to be aware that he was humping you, almost as if subconsciously he was trying to show you what sex could be like.

“De.” You say feeling the pressure building up once more but not from your breasts this time.

“ _Fuck_ ” He barely whispered the curse, knowing what you were trying to say to him, feeling it in the hastiness of your hips. “Princess, just let go for me, its normal to feel this way, all that pressure being released can be very intense and this can be the only form to express it sometimes.” He said not believing a word he just said but trying to keep up with the excuse that had started it all. Rubbing your nipples and then placing his lips back on them, doubling his efforts even though he was taken back by how close you already were to the edge.

Nails pulling at his hair, bringing him further into your chest, smothering him with your leaky breasts. Head going back and hips chasing something more. His hand moved to your covered clit, giving you what you needed and rubbing you through the shorts you had on. Something snapping inside of you as he finally touched your core, a loud moan tearing through you as he just swallowed around your breast, watching you through hooded eyes as you fell apart for him.

Allowing you a few moments to settle before taking his lips off you, replacing them with his hands, he pinches them hard as milk slipped out all over his fingers, splashing everywhere. You didn’t notice though, still out of it from the pleasure. His hips start grinding up into yours, groaning as his jeans kept sliding against your soaked through shorts, creating a wet spot over his erection, while giving your breasts his constant attention. Feeling dazed, your attention coming back slowly, you start feeling his body against yours, a sense of protection, love, and safety flowing through you as you lay wrapped up in his arms. Not being able to pay any attention to detail until your brain cleared the fogginess.

He felt your hips start grinding again, and like most of the night you were not even consciously aware of it, you were in your own little world still. Not do anything further though, just grinding against your lips, overstimulating you a bit but helping your boobs feel the best they’ve felt in a while. He honestly was enjoying the taste as well and would happily do this for you for hours if you asked.

“De, inside.” You manage, groaning as you could feel his package against your lips, throbbing against you through his jeans and your wet shorts. He loses his rhythm, mouth dropping your nipple in surprise, he would’ve never thought you’d want to go further than you already had. Not wanting you to regret this he looks into your eyes, seeing the desire and trust in them even if they do look a bit glossy. He lifts you slightly and shuffles out of his jeans and boxers the best he can until his cock pops out. You don’t see it but you can sure as hell feel it against you, the barrier of your flimsy shorts doing nothing to stop the feeling of his erection against your heat. He doesn’t go to make a further move though, just staring up at you and you know what he’s doing, he wants to be sure you want this and that he’s not pressuring you. Not wanting to stop, you take charge, moving your shorts to the side and grabbing his hardon and slipping him right inside.

“Ahh”, your hand reaches into his hair and the other around his shoulders resting on his back, legs wound against his waist. Slowly he begins moving you back and forth, having you grind on him until you feel comfortable enough to really let him fuck you. Leaning up to bite at your neck and leave kisses down your throat making their way back to your nipples, needing your sweet milk again.

“So good, good boy.” You moan incoherently. Feeling so dazed with everything going on, your eyes are shut tight and a hand placed firmly in his hair. Dean stutters his pace, throbbing inside you, you clench tightly in response, he was happy you weren’t focused on his face to know how much those words affected him. Instead, he just increased his pace, starting to bounce you down onto his length, balls hitting your ass each time.

“Fuck baby, I’m close.” You let him know, starting to move your own hips to meet his. These baby hormones were killing you in the worst and best way, they had you so far on the edge in such a short time, it had you feeling jittery and charged up.

“Go on sweetheart.” He says lips coming off your nipple but maintaining pressed against your breasts. Your hand dragging his head toward yours, letting your lips meet his. He stilled for a moment, shocked at your sudden actions even though he was deep inside of you, it didn’t take long for him to respond, returning your kisses with eagerness. It was intimate and gentle, but you needed more to get you there, sliding your tongue against his lips, he opens up allowing you to explore instead of fighting for dominance the way his brain told him too. Biting his lip when your done, you release him and drag him back down to your nipples. His lips latch back on and suck, “yes, good boy suck me dry, shit, De.”

One last thrust has you coming undone, clenching down and wrapping yourself around him. Your mouth falls open, but no sound comes out as you shake on top of him, he doesn’t stop his thrusts, working you through your high. The aftershocks remain for longer than usual, making you feel relaxed and sated, as you lay your face in the crook of Dean’s neck. He continues his movements rocking inside of you, allowing you to collect yourself but needing the sensation to ease his boner as well.

When you feel ready you start rocking down into him, soon enough meeting him thrust for thrust as you bounced yourself on him and he fucked up into you. The moment his pace started faltering you know he’s close, your breathless fucked out voice whispers in his ear “Cum for me big brother, drink up all that yummy milk and cum inside your little sister.”

“Fuck Y/n.” he moans thrusting hard into you and holding tight, one hand on your shoulder pressing you down as he pushes up, the other wrapped around your waist as he finally unloads inside of you. Slumping against you, head buried in your chest as you rake your hand through his hair letting him come down from his orgasm. When he can finally move again, he lifts his head and sees some drops of milk form on your nipple and start dripping, he latches back onto the nipple, licking at it gently.

“Mmm, too sensitive.” You moan but push your chest into him anyway, walls fluttering around his length, causing him to let out a low growl.

“Don’t worry princess, just cleaning you up a bit. I plan to give you a break before we go again.”

“Again?”

“Of course, princess. I’m going to help you anytime you need while we’re in quarantine and I don’t think we’ve relieved all your pain for the day, but trust me your boobs will feel so much better after I milk you dry. Especially after I do it a couple hundred times.”

**Author's Note:**

> Comments and kudos are appreciated! If you ever want to chat, have suggestions or have any NSFW gifs, go here, [My Tumblr](https://omgspnfanfiction.tumblr.com/post/184996739213/masterlist)
> 
> If you enjoy my fics and have a couple of extra dollars to spare, [Treat Me To A Tea, Please](https://omgspnfanfiction.tumblr.com/post/633740858962984960/please-help-if-you-can)


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